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Methanol → 2-[3-(Phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-1-yl]ethylamine dihydrochloride

HRID 731561
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HRID 731561 반응식
[C:1]1([S:7]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[CH:16][CH:17]=3)[N:12]([CH2:19][CH2:20][N:21]3C(=O)C4C(=CC=CC=4)C3=O)[CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.NN.CO.C(Cl)[Cl:37]>O1CCOCC1>[ClH:37].[ClH:37].[C:1]1([S:7]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[CH:16][CH:17]=3)[N:12]([CH2:19][CH2:20][NH2:21])[CH:11]=2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
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6

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HCID 887MethanolHCID 6344DichloromethaneHCID 9321HydrazineHCID 220281762-{2-[3-(Phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-1-yl]ethyl}-1H-isoindole-1,3(2H)-dione

생성물 1

HCID 220281972-[3-(Phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-1-yl]ethylamine dihydrochloride

시약·촉매·용매 1

HCID 31275
1,4-Dioxane
용매

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온도
50 °C

실험 절차

A solution of 2-{2-[3-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-1-yl]ethyl}-1H-isoindole-1,3(2H)-dione (4.54 g, 10.5 mmol) in dioxane is treated with anhydrous hydrazine (8.3 mL, 265 mmol), heated at 50° C. for 3 h, concentrated in vacuo, diluted with water and extracted with CH2Cl2. The combined extracts are dried over MgSO4 and concentrated in vacuo to give a clear gum residue. Chromatography (1:9 methanol:CH2Cl2) of the residue affords the free amine of the title compound as a clear gum. The free amine is dissolved in ethanol, acidified with 2N aqueous HCl and concentration in vacuo. Crystallization of the resultant residue from ethanol/ether affords the title compound as a white solid, 3.20 g, mp 195-197° C., characterized by mass spectral and HNMR analyses.

후처리

  1. concentrationconcentrated in vacuo
  2. additiondiluted with water
  3. extractionextracted with CH2Cl2
  4. dry with materialThe combined extracts are dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto give a clear gum residue

출처 및 근거

ORD 기록
ord-3dc4a99f54f54dc0b99de3748c61c089
출처 데이터셋
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07585873B2

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